enniatin B2

Details

• Internal ID: 7123f002-a7be-4639-ac56-7df5d98b46a4
• Taxonomy: Organic acids and derivatives > Peptidomimetics > Depsipeptides > Cyclic depsipeptides
• IUPAC Name: (3S,6R,9S,12R,15S,18R)-4,10-dimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• SMILES (Canonical): CC(C)C1C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N(C(C(=O)OC(C(=O)N1)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
• SMILES (Isomeric): CC(C)[C@H]1C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
• InChI: InChI=1S/C32H55N3O9/c1-15(2)21-30(39)43-25(19(9)10)28(37)35(14)23(17(5)6)32(41)44-26(20(11)12)29(38)34(13)22(16(3)4)31(40)42-24(18(7)8)27(36)33-21/h15-26H,1-14H3,(H,33,36)/t21-,22-,23-,24+,25+,26+/m0/s1
• InChI Key: NUFASKQIWTXKBR-LZNKSJHBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₅N₃O₉
• Molecular Weight: 625.80 g/mol
• Exact Mass: 625.39383034 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 6.40
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• 632-91-7
• (3S,6R,9S,12R,15S,18R)-4,10-dimethyl-3,6,9,12,15,18-hexa(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CHEMBL504435
• DTXSID501017635
• (3S,6R,9S,12R,15S,18R)-3,6,9,12,15,18-hexaisopropyl-4,10-dimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4834	48.34%
Caco-2	-	0.7345	73.45%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Lysosomes	0.4774	47.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9076	90.76%
OATP1B3 inhibitior	+	0.9397	93.97%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9441	94.41%
P-glycoprotein inhibitior	+	0.6368	63.68%
P-glycoprotein substrate	-	0.5711	57.11%
CYP3A4 substrate	-	0.5465	54.65%
CYP2C9 substrate	+	0.5963	59.63%
CYP2D6 substrate	-	0.8895	88.95%
CYP3A4 inhibition	-	0.9587	95.87%
CYP2C9 inhibition	-	0.9131	91.31%
CYP2C19 inhibition	-	0.9180	91.80%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.9292	92.92%
CYP2C8 inhibition	-	0.9833	98.33%
CYP inhibitory promiscuity	-	0.9904	99.04%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7907	79.07%
Carcinogenicity (trinary)	Non-required	0.6682	66.82%
Eye corrosion	-	0.9722	97.22%
Eye irritation	-	0.9171	91.71%
Skin irritation	-	0.8026	80.26%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4875	48.75%
Micronuclear	+	0.7800	78.00%
Hepatotoxicity	+	0.6801	68.01%
skin sensitisation	-	0.9258	92.58%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5212	52.12%
Nephrotoxicity	+	0.4766	47.66%
Acute Oral Toxicity (c)	III	0.4676	46.76%
Estrogen receptor binding	+	0.6832	68.32%
Androgen receptor binding	+	0.5208	52.08%
Thyroid receptor binding	+	0.6163	61.63%
Glucocorticoid receptor binding	-	0.5063	50.63%
Aromatase binding	+	0.5543	55.43%
PPAR gamma	+	0.5759	57.59%
Honey bee toxicity	-	0.8771	87.71%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	-	0.8194	81.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.89%	97.25%
CHEMBL4072	P07858	Cathepsin B	93.93%	93.67%
CHEMBL1949	P62937	Cyclophilin A	93.51%	98.57%
CHEMBL5103	Q969S8	Histone deacetylase 10	93.29%	90.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.37%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.86%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.16%	95.56%
CHEMBL255	P29275	Adenosine A2b receptor	86.91%	98.59%
CHEMBL3837	P07711	Cathepsin L	85.75%	96.61%
CHEMBL333	P08253	Matrix metalloproteinase-2	85.03%	96.31%
CHEMBL3310	Q96DB2	Histone deacetylase 11	84.34%	88.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.95%	85.14%
CHEMBL321	P14780	Matrix metalloproteinase 9	82.83%	92.12%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.24%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	81.67%	94.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.27%	99.23%

Plants that contains it

• Alcea rosea
• Alpinia roxburghii
• Balanops australiana
• Davallia perdurans
• Euonymus tingens
• Euphorbia cornigera
• Gonzalezia decurrens
• Hylocomium splendens
• Kokoona reflexa
• Maesa ramentacea
• Millettia laurentii
• Monodora tenuifolia
• Ocimum tenuiflorum
• Pinus strobus
• Pinus sylvestris
• Pluchea odorata
• Salacia lehmbachii
• Salvia yosgadensis
• Sideritis brevibracteata
• Sideroxylon cubense

Cross-Links

• PubChem: 44559513
• NPASS: NPC246005
• LOTUS: LTS0160715
• wikiData: Q105185845